Meta-bis anilide derivatives and their utility as herbicides

ABSTRACT

Compounds corresponding to the formula:

This is a division of application Ser. No. 20,104 filed Mar. 16, 1970,now abandoned, which application is a continuation-in-part of copendingapplication Ser. No. 741,267, filed July 1, 1968 now abandoned, which inturn is a continuation-in-part of application Ser. No. 659,865, filedAug. 11, 1967, now abandoned.

This invention relates to herbicidally active meta-bis anilidederivatives. More specifically, this invention relates to certain newcompounds and the use as active herbicidal substances of certainsubstituted meta-bis-anilides.

The novel compounds of the present invention correspond to the generalformula: ##SPC2##

In which R₁ and R₂ are independently selected from the group consistingof hydrogen, alkyl, alkoxyalkyl, cycloalkyl, pinonoyl, ethylcycloalkyl,lower alkenyl, halogenated lower alkyl, benzyl, furyl, ethylphenyl,2,4-dichlorophenoxy-methylene, styryl, phenyl, and substituted-phenyl inwhich said substituents are nitro, halogen, methyl or methoxy; selectedfrom the group consisting of hydrogen and lower alkyl; X and Y areindependently oxygen or sulfur; and Z is selected from the groupconsisting of halogen, nitro, amino, lower alkyl, lower alkoxy, andtrifluoromethyl and n is an integer having a value from 0 to 4.

The method of the present invention of controlling undesirablevegetation comprises applying an herbicidally effective amount of theabove represented compounds to the area where control is desired.Compounds wherein R₁ and R₂ are independently selected from the groupconsisting of alkyl, hydrogen, alkoxyalkyl, cycloalkyl, pinonoyl,ethylcycloalkyl, lower alkenyl, halogenated lower alkyl, benzyl,2,4-dichlorophenoxymethylene, styryl, phenyl, phenyl and substitutedphenyl in which the substituents are nitro, halogen, methyl or methoxy;R₃ and R₄ are independently selected from the group consisting ofhydrogen and lower alkyl; X and Y are independently oxygen or sulfur;and Z is selected from the group consisting of halogen, nitro, amino,lower alkyl, lower alkoxy, and trifluoromethyl and n is an integerhaving a value from 0 to 4; are within the scope of this aspect of thepresent invention.

The term alkyl, preferably includes those members of the group whichcontains from 1 through about 10 carbon atoms, inclusive, in bothstraight chain and branched chain configurations. The term lower alkyland lower alkoxy preferably include members of the groups having from 1through about 6 carbon atoms, inclusive. The term alkoxyalkyl includesmembers having 2 to 4 carbon atoms. The term cycloalkyl preferablyincludes members of the group having from 3 through about 6 carbonatoms, inclusive. The term lower alkenyl preferably includes thosemembers of the group containing at least one double bond and containingfrom 2 to 4 carbon atoms, inclusive.

In its most preferred form, the invention relates to compositions havingthe formula ##SPC3##

in which R₁ and R₂ independently are hydrogen, alkyl containing from 1to 10 carbon atoms, inclusive, alkoxyalkyl containing 2 to 4 carbonatoms, cycloalkyl containing from 3 to 6 carbon atoms, inclusive,pinonoyl, ethylcycloalkyl wherein the cycloalkyl moiety contains from 5to 6 carbon atoms, inclusive, lower alkenyl containing from 2 to 6carbon atoms, inclusive, halogenated lower alkyl containing 1 to 6carbon atoms, inclusive, benzyl, furyl, ethylphenyl, styryl,2,4-dichlorophenoxy-methylene, phenyl and substituted phenyl in whichsaid substituents are nitro, halogen, especially chlorine and fluorine,methyl, and methoxy; and Z is hydrogen, 4'-chloro, 3'-chloro or2'-methyl.

The compounds of this invention are prepared by one of several generalmethods. One such general method is the condensation between theappropriate m-phenylene diamine and an appropriate acid anhydride orchloride to prepare the desired meta-bis-symmetrically substitutedanilide. Another general method is the condensation between theappropriate m-mono-substituted amino anilide and an appropriate acideanhydride or acid chloride to prepare the desiredmeta-bis-assymetrically substituted anilide. The reactions proceedreadily in the liquid phase. The employment of a solvent is also useful,facilitating processing, as well as agitation of the reactants. Whenusing a starting material containing an acid chloride, it is preferredto carry out the reaction in the presence of a hydrogen halide acceptorsuch as triethylamine, pyridine, picoline, sodium carbonate and thelike. The reactions are preferably carried out at temperatures thatpermit operation in the liquid phase.

Compounds of the present invention are prepared in accordance with thefollowing illustrative examples.

EXAMPLE 1 Preparation of Meta-bis-isobutyranilide

Isobutyric anhydride, 26g. (0.16 mole) is added slowly to 8.6g. (0.08mole) of m-phenylene diamine in an open beaker. The mixture was stirred.The solid product is washed consecutively with water, sodium bicarbonatesolution and ether. After drying, there is obtained 18.5g. (92 percentof theory) of the title compound, m.p. 205°-206° C.

The following compounds are typical of those prepared using the methodof the foregoing example: m-bis-acetanilide, m-bis-propionanilide,m-bis-n-butyranilide and m-bis-trifluoroacetanilide.

EXAMPLE 2 Preparation of Meta-bis-2,2-dimethyl-valeranilide

Meta-phenylene diamine, 87g. (0.8 moles), is dissolved in one liter ofacetone containing 190g. (1.9 moles) of triethylamine. To this solution,2,2-dimethylvaleryl chloride, 260g. (1.75 moles) is added slowly withstirring. The reaction flask is cooled in a cold water bath. Theresulting mixture is poured into 1-liter of cold water and the resultingoil crystallized. The product is further washed with water, then 5percent hydrochloric acid solution, followed by 5 percent sodiumhydroxide solution and finally water. The product is dried. There isobtained 256g. (96 percent of theory) of the title compound, m.p.109°-111° C.

The following compounds are typical of those prepared using the methodof the foregoing example: m-bis-pivalanilide,m-bis-3,3-dimethylbutyranilide, m-bis-crotonanilide, m-bis-hexanilide,and m-bis-isovalerylanilide.

EXAMPLE 3 Preparation of Meta-propionamido isobutyranilide

Meta-amino propionanilide, 11.5g. (0.07 moles) is treated withisobutyric anhydride, 11.1g. (0.07 moles) is an open beaker. The productis poured into water and washed with 5 percent hydrochloric acidsolution, 5 percent sodium hydroxide solution, and water. The product isdried of water. There is obtained 15.2g. (93 percent of theory) of thetitle compound, m.p. 174°-175° C.

The following compounds are typical of those prepared using the methodof the foregoing example: m-propionamido trifluoroacetanilide,m-propionamido butyranilide, m-isobutyramido trifluoroacetanilide andm-isobutyramido butyranilide.

EXAMPLE 4 Preparation of Meta-propionamido cyclopropane carboxanilide

Meta-aminopropionanilide, 13.1g. (0.08 mole) is dissolved in 200 ml. ofa 50/50 v/v mixture of glacial acetic acid and saturated sodium acetatesolution. To this solution is added 9.2g. (0.088 moles) of cyclopropanecarbonyl chloride. The chloride is added slowly with adequate stirringand cooling. The product, which crystallizes from the solution, iscollected by filtration. The product is consecutively washed with a 5percent solution of sodium hydroxide, a 5 percent solution ofhydrochloric acid and water. After washing, the crystals are dried.There is obtained 15g. (81 percent of theory) of the title compound,m.p. 185°-186° C.

The following compounds are typical of those prepared using the methodof the foregoing example: m-propionamido cyclohexanecarboxanilide,m-propionamido phenyl-acetanilide, m-propionamido crotonanilide, andm-propionamido furoanilide.

EXAMPLE 5 Preparation of Meta-propionamido-3,3-dimethyl butylanilide

Meta-aminopropionanilide, 180g. (1.1 moles) is dissolved in 500 ml. ofacetone containing 126g. of triethylamine. To this solution is added164g. (1.22 moles) of 3,3-dimethyl butyryl chloride. The chloride isadded slowly and the reaction mixture is adequately stirred and cooled,with an ice bath. The mixture is poured into water and consecutivelywashed with 5 percent hydrochloric acid solution, 5 percent sodiumhydroxide solution, and water. After washing, the material is dried.There is obtained 178g. (62 percent of theory) of the title compound,m.p. 179.5° - 181.5° C.

The following compounds are typical of those prepared using the methodof the foregoing example: m-propionamido-2,2-dimethyl valeranilide,m-propionamido-2 ethyl butyranilide, m-propionamido pivalanilide, andm-pivalamino-2-2-dimethyl valeranilide.

The following is a table of the compounds which are prepared accordingto the aforedescribed procedures. Compound numbers have been assigned tothem and are used for identification throughout the balance of thespecification.

                                      TABLE I                                     __________________________________________________________________________    Compound                                                                      Number                                                                              X Y R.sub.1      R.sub.2      R.sub.3                                                                          R.sub.4                                                                         Z   m.p. °C.                  __________________________________________________________________________    1     0 0 C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                                            H  H     174-175                          2     0 0 furyl        furyl        H  H     191-194                          3     0 0 CH.sub.3     CH.sub.3     H  H     186-188                          4     0 0 CH.sub.3     C.sub.2 H.sub.5                                                                            H  H     239-243                          5     0 0 CH.sub.3     i-C.sub.3 H.sub.7                                                                          H  H     165-167                          6     0 0 n-C.sub.3 H.sub.7                                                                          n-C.sub.3 H.sub.7                                                                          H  H     142.5-143                        7     0 0 i-C.sub.3 H.sub.7                                                                          i-C.sub.3 H.sub.7                                                                          H  H     205-206                          8     0 0 C.sub.2 H.sub.5                                                                            CCl.sub.3    H  H     159-161                          9     0 0 H            H            H  H     152-154                          10    0 0 C.sub.2 H.sub.5                                                                            CH.sub.2 Cl  H  H     164-167                          11    0 0 C.sub.2 H.sub.5                                                                            CF.sub.3     H  H     196-197                          12    0 0 C.sub.2 H.sub.5                                                                            C.sub.3 H.sub.7                                                                            H  H     156-157                          13    0 0 C.sub.2 H.sub.5                                                                            i-C.sub.3 H.sub.7                                                                          H  H     174-175.5                        14    0 0 C.sub.2 H.sub.5                                                                            cyclopropyl  H  H     186-188                          15    0 0 C.sub.2 H.sub.5                                                                            i-C.sub.4 H.sub.9                                                                          H  H     130-131                          16    0 0 C.sub.2 H.sub.5                                                                            n-C.sub.5 H.sub.11                                                                         H  H     173-178                          17    0 0 CH.sub.2 Cl  CH.sub.2 Cl  H  H     211-212                          18    0 0 CHCl.sub.2   CHCl.sub.2   H  H     158-160                          19    0 0 CH.sub.2 CH.sub.2 Cl                                                                       CH.sub.2 CH.sub.2 Cl                                                                       H  H     160-163                          20    0 0 CH=CH.sub.2  CH=CH.sub.2  H  H     167-170                          21    0 0 CH=CHCH.sub.3                                                                              CH=CHCH.sub.3                                                                              H  H     215-217.5                        22    0 0 cyclopropyl  cyclopropyl  H  H     217-221                          23    0 0 i-C.sub.4 H.sub.9                                                                          i-C.sub.4 H.sub.9                                                                          H  H     226-230                          24    0 0 n-C.sub.5 H.sub.11                                                                         n-C.sub.5 H.sub.11                                                                         H  H     122-125                          25    0 0 n-C.sub.6 H.sub.13                                                                         n-C.sub.6 H.sub.13                                                                         H  H     109-113                          26    0 0 cyclohexyl   cyclohexyl   H  H     210-212.5                        27    0 0 benzyl       benzyl       H  H     194-197                          28    0 0 CCl.sub.3    CCl.sub.3    H  H     204-207                          29    0 0 C(CH.sub.3).sub.2 Br                                                                       C(CH.sub.3).sub.2 Br                                                                       H  H     126-128                          30    0 0 t-C.sub.4 H.sub.9                                                                          t-C.sub.4 H.sub.9                                                                          H  H     188-189                          31    0 0 CH(C.sub.2 H.sub.5).sub.2                                                                  CH(C.sub.2 H.sub.5).sub.2                                                                  H  H     148-151                          32    0 0 phenyl       phenyl       H  H     234-237.5                        33    0 0 3-NO.sub.2 -phenyl                                                                         3-NO.sub.2 -phenyl                                                                         H  H     250-255                          34    0 0 C.sub.2 H.sub.5                                                                            CHCl.sub.2   H  H     159-163                          35    0 0 CH=CH.sub.2  C.sub.2 H.sub.5                                                                            H  H     165-166.5                        36    0 0 C.sub.2 H.sub.5                                                                            CH.sub.2 CH.sub.2 Cl                                                                       H  H     139-142                          37    0 0 C.sub.2 H.sub.5                                                                            CH=CHCH.sub.3                                                                              H  H     183-186                          38    0 0 C.sub.2 H.sub.5                                                                            C(CH.sub.3).sub.2 Br                                                                       H  H     165-167                          39    0 0 C.sub.2 H.sub.5                                                                            n-C.sub.6 H.sub.13                                                                         H  H     256-260                          40    0 0 C.sub.2 H.sub.5                                                                            furyl        H  H     151-152.5                        41    0 0 C.sub.2 H.sub.5                                                                            cyclohexyl   H  H     300-304                          42    0 0 C.sub.2 H.sub.5                                                                            phenyl       H  H     210-213                          43    0 0 C.sub.2 H.sub.5                                                                            3-NO.sub.2 -phenyl                                                                         H  H     198-201                          44    0 0 C.sub.2 H.sub.5                                                                            benzyl       H  H     129-130                          45    0 0 i-C.sub.3 H.sub.7                                                                          cyclopropyl  H  H     184-187                          46    0 0 i-C.sub.3 H.sub.7                                                                          CH=CH.sub.2  H  H     186-190                          47    0 0 i-C.sub.3 H.sub.7                                                                          n-C.sub.4 H.sub.9                                                                          H  H     124-126                          48    0 0 i-C.sub.3 H.sub.7                                                                          i-C.sub.4 H.sub.9                                                                          H  H     141-143                          49    0 0 i-C.sub.3 H.sub.7                                                                          furyl        H  H     152-154                          50    0 0 i-C.sub.3 H.sub.7                                                                          cyclohexyl   H  H     142-145                          51    0 0 i-C.sub.3 H.sub.7                                                                          phenyl       H  H     152-153                          52    0 0 i-C.sub.3 H.sub.7                                                                          3-NO.sub. 2 -phenyl                                                                        H  H     156-161                          53    0 0 CHClCH.sub.3 CHClCH.sub.3 H  H     169.5-173                        54    0 0 C(CH.sub.3)=CH.sub.2                                                                       C(CH.sub.3)=CH.sub.2                                                                       H  H     139-141                          55    0 0 C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          H  H     96-100                           56    0 0 CHClCH.sub.3 C.sub.2 H.sub.5                                                                            H  H     164-166                          57    0 0 C.sub.2 H.sub.5                                                                            C(CH.sub.3)=CH.sub.2                                                                       H  H     154-157                          58    0 0 i-C.sub.3 H.sub.7                                                                          CH.sub.2 Cl  H  H     205-209                          59    0 0 i-C.sub.3 H.sub.7                                                                          CHCl.sub.2   H  H     178-180.5                        60    0 0 i-C.sub.3 H.sub.7                                                                          CCl.sub.3    H  H     160-162                          61    0 0 i-C.sub.3 H.sub.7                                                                          CHClCH.sub.3 H  H     168-172                          62    0 0 i-C.sub.3 H.sub.7                                                                          CH.sub.2 CH.sub.2 Cl                                                                       H  H     179-183                          63    0 0 i-C.sub.3 H.sub.7                                                                          CH=CHCH.sub.3                                                                              H  H     157-160                          64    0 0 i-C.sub.3 H.sub.7                                                                          C(CH.sub.3)=CH.sub.2                                                                       H  H     156-159                          65    0 0 i-C.sub.3 H.sub.7                                                                          n-C.sub.3 H.sub.7                                                                          H  H     146-148.5                        66    0 0 i-C.sub.3 H.sub.7                                                                          C(CH.sub.3).sub.2 Br                                                                       H  H     151-153                          67    0 0 i-C.sub.3 H.sub.7                                                                          n-C.sub.5 H.sub.11                                                                         H  H     122-126                          68    0 0 i-C.sub.3 H.sub.7                                                                          CH(C.sub.2 H.sub.5).sub.2                                                                  H  H     157-158                          69    0 0 i-C.sub.3 H.sub.7                                                                          n-C.sub.6 H.sub.13                                                                         H  H     114-116                          70    0 0 i-C.sub.3 H.sub.7                                                                          benzyl       H  H     164-167                          71    0 0 CF.sub.3     CF.sub.3     H  H     207-211                          72    0 0 CH.sub.2 C(CH.sub.3).sub.3                                                                 C.sub.2 H.sub.5                                                                            H  H     177-179                          73    0 0 2,4-diCl-phenyl                                                                            C.sub.2 H.sub.5                                                                            H  H     210-212                          74    0 0 3,4-diCl-phenyl                                                                            C.sub.2 H.sub.5                                                                            H  H     175-177                          75    0 0 4-NO.sub.2 -phenyl                                                                         C.sub.2 H.sub.5                                                                            H  H     227-230                          76    0 0 CH.sub.2 C(CH.sub.3).sub.2                                                                 i-C.sub.3 H.sub.7                                                                          H  H     151-153                          77    0 0 2,4-diCl-phenyl                                                                            i-C.sub.3 H.sub.7                                                                          H  H     186-188                          78    0 0 3,4-diCl-phenyl                                                                            i-C.sub.3 H.sub.7                                                                          H  H     189-191                          79    0 0 C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          C.sub.2 H.sub.5                                                                            H  H     112-115                          80    0 0 CH(C.sub.2 H.sub.5)                                                                        C.sub.2 H.sub.5                                                                            H  H     153-157                          81    0 0 t-C.sub.4 H.sub.9                                                                          C.sub.2 H.sub.5                                                                            H  H     177-179                          82    0 0 CCl.sub.3    t-C.sub.4 H.sub.9                                                                          H  H     169-173                          83    0 0 C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          t-C.sub.4 H.sub.9                                                                          H  H     119-120                          84    0 0 CF.sub.3     t-C.sub.4 H.sub.9                                                                          H  H     >300                             85    0 0 C(CH.sub.3).sub.2 C.sub.6 H.sub.13                                                         t-C.sub.4 H.sub.9                                                                          H  H     95-101                           86    0 0 C(CH.sub.3).sub.2 C.sub.6 H.sub.13                                                         C(CH.sub.3).sub.2 C.sub.6 H.sub.13                                                         H  H     94-98                            87    0 0 CCl.sub.2 CH.sub.3                                                                         CCl.sub.2 CH.sub.3                                                                         H  H     135.5-137.5                      88    0 0 CCl.sub.2 CH.sub.3                                                                         C.sub.2 H.sub.5                                                                            H  H     163-165                          89    0 0 CH.sub.2 C(CH.sub.3).sub.3                                                                 CH.sub.2 C(CH.sub.3).sub. 3                                                                H  H     187-190.5                        90    0 0 CCl.sub.3    CH.sub.2 C(CH.sub.3).sub.3                                                                 H  H     176-180                          91    0 0 CCl.sub.3    CH.sub.2 C(CH.sub.3).sub.3                                                                 H  H     177-180                          92    0 0 CF.sub.3     CH.sub.2 C(CH.sub.3).sub.3                                                                 H  H     200-201                          93    0 0 CCl.sub.2 CH.sub.3                                                                         CH.sub.2 C(CH.sub.3).sub.3                                                                 H  H     155.5-159                        94    0 0 C(CH.sub.3).sub.3                                                                          CH.sub.2 C(CH.sub.3).sub.3                                                                 H  H     184-185                          95    0 0 C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          CH.sub.2 C(CH.sub.3).sub.3                                                                 H  H     105-110                          96    0 0 C(CH.sub.3).sub.2                                                                          C.sub.3 H.sub.7                                                                            H  H     133-134                          97    0 0 CF.sub.3     C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          H  H     117-120                          98    0 0 CCl.sub.3    C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          H  H     119-122                          99    0 0 C(CH.sub.3).sub.2 Br                                                                       C.sub.2 H.sub.5                                                                            H  H     144-147                          100   0 0 CH=C(CH.sub.3).sub.2                                                                       C.sub.2 H.sub.5                                                                            H  H     66-72                            101   0 0 CH(C.sub.2 H.sub.5).sub.2                                                                  C.sub.2 H.sub.5                                                                            H  H     155.5-156                        102   0 0 CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                       C.sub.2 H.sub.5                                                                            H  H     127-130                          103   0 0 CH.sub.2 OCH.sub.3                                                                         CH.sub.2 C(CH.sub.3).sub.3                                                                 H  H     n.sub.D.sup.30 =1.5441           104   0 0 CH=C(CH.sub.3).sub.2                                                                       CH=C(CH.sub.3).sub.2                                                                       H  H     (glass)                          105   0 0 CH=C(CH.sub.3).sub.2                                                                       C(CH.sub.3).sub.3                                                                          H  H     112-117                          106   0 0 CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                       C(CH.sub.3).sub.3                                                                          H  H     109-112                          107   0 0 CH=C(CH.sub.3).sub.2                                                                       C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          H  H     (glass)                          108   0 0 CH.sub.2 CH(CH.sub.3)CH.sub.2 C(CH.sub.3).sub.3                                            C.sub.2 H.sub.5                                                                            H  H     108-111                          109   0 0 CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                       CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                       H  H     150-152                          110   0 0 CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                       C(CH.sub.3).sub.2 H.sub.7                                                                  H  H     114.116                          111   0 0 CH.sub.2 CH(CH.sub.3)CH.sub.2 C(CH.sub.3).sub.3                                            C(CH.sub.3).sub.3                                                                          H  H     48-51                            112   0 0 CH.sub.2 CH(CH.sub.3)CH.sub.2 C(CH.sub.3).sub.3                                            C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          H  H     (glass)                          113   0 0 CH(CH.sub.3)C.sub.2 H.sub.5                                                                C.sub.2 H.sub.5                                                                            H  H     150-151                          114   0 0 CH(CH.sub.3)C.sub.2 H.sub.5                                                                CH(CH.sub.3)C.sub.2 H.sub.5                                                                H  H     159-161                          115   0 0 CH(CH.sub.3)C.sub.2 H.sub.5                                                                C(CH.sub.3).sub.3                                                                          H  H     169-171                          116   0 0 CH.sub.2 C(CH.sub.3).sub.3                                                                 CH(CH.sub.3)C.sub.2 H.sub.5                                                                H  H     146-149                          117   0 0 CF.sub.3     CH(CH.sub.3)C.sub.2 H.sub.5                                                                H  H     157-158                          118   0 0 2-Cl-phenyl  C.sub.2 H.sub.5                                                                            H  H     143.5-144.5                      119   0 0 4-Cl-phenyl  C.sub.2 H.sub.5                                                                            H  H     223-224.5                        120   0 0 2-CH.sub.3 O-phenyl                                                                        C.sub.2 H.sub.5                                                                            H  H     124-125                          121   0 0 4-CH.sub.3 O-phenyl                                                                        C.sub.2 H.sub.5                                                                            H  H     223-224                          122   0 0 4-CH.sub.3 -phenyl                                                                         C.sub.2 H.sub.5                                                                            H  H     211-212                          123   0 0 4-Cl-phenyl  C(CH.sub.3).sub.3                                                                          H  H     191-195                          124   0 0 benzyl       C(CH.sub.3).sub.3                                                                          H  H     164-165                          125   0 0 benzyl       CH(CH.sub.3)C.sub.2 H.sub.5                                                                H  H     161-163                          126   0 0 benzyl       CH(CH.sub.3)C.sub.3 H.sub.7                                                                H  H     149.5-151                        127   0 0 benzyl       C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          H  H     142-143.5                        128   0 0 styryl       C.sub.2 H.sub.5                                                                            H  H     160-163                          129   0 0 --CH.sub.2 CH.sub.3                                                                        CH(CH.sub.3).sub.2                                                                         H  H 4'-Cl                                                                             161-162                          130   0 0 C(CH.sub.3).sub.3                                                                          CH(CH.sub.3).sub.2                                                                         H  H 4'-Cl                                                                             176.5-178.5                      131   0 0 CH.sub.2 C(CH.sub.3).sub.3                                                                 CH(CH.sub.3).sub.2                                                                         H  H 4'-Cl                                                                             194-194.5                        132   0 0 CCl.sub.3    CH(CH.sub.3).sub.2                                                                         H  H 4'-Cl                                                                             156-158                          133   0 0 benzyl       CH(CH.sub.3).sub.2                                                                         H  H 4'-Cl                                                                             211-212                          134   0 0 C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                                  H     132-133                          135   0 0 CH.sub.2 C(CH.sub. 3).sub.3                                                                C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                                  H     178.5-180                        136   0 0 CH.sub.2 OCH.sub.3                                                                         C(CH.sub.3).sub.3                                                                          H  H     108-109                          137   0 0 CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                       C(CH.sub.3).sub.3                                                                          H  H     115-116                          138   0 0 CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                       CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                       H  H     151-153                          139   0 0 CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                       C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          H  H     121-123                          140   0 0 CH.sub.2 CH.sub.2 --phenyl                                                                 CH.sub.2 C(CH.sub.3).sub.3                                                                 H  H     101-107                          141   0 0 C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5 C(CH.sub.3).sub.3                                                          H  H     178-179                          142   0 0 CH.sub.2 CH.sub.2 C(CH.sub.3).sub.3                                                        CH(CH.sub.3)C.sub.3 H.sub.7                                                                H  H     75-77                            143   0 0 CH.sub.2 CH.sub.2 C(CH.sub.3).sub.3                                                        CH.sub.2 C(CH.sub.3).sub.3                                                                 H  H     184-185                          144   0 0 CH.sub.2 CH.sub.2 C(CH.sub.3).sub.3                                                        CH.sub.2 CH.sub.2 C(CH.sub.3 ).sub.3                                                       H  H     216-218                          145   0 0 CH.sub.2 CH.sub.2 C(CH.sub.3).sub.3                                                        C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          H  H     151-153                          146   0 0 C(CH.sub.3).sub.2 CH.sub.2 Cl                                                              C(CH.sub.3).sub.2 CH.sub.2 Cl                                                              H  H     145-150                          147   0 0 C(CH.sub.3).sub.2 CH.sub.2 Cl                                                              C.sub.2 H.sub.5                                                                            H  H     161-164                          148   0 0 C(CH.sub.3).sub.2 CH.sub.2 Cl                                                              C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          H  H     110-112                          149   0 0 C.sub.2 H.sub.5                                                                            CH.sub.2 O-2,4-diCl-phenyl                                                                 H  H     206-207                          150   0 0 CH.sub.2 CH=CH.sub.2                                                                       C.sub.2 H.sub.5                                                                            H  H     135-139                          151   0 0 CH.sub.2 CH=CH.sub.2                                                                       CH.sub.2 CH=CH.sub.2                                                                       H  H     99-108                           152   0 0 C(CH.sub.3)=CH.sub.2                                                                       C(CH.sub.3).sub.3                                                                          H  H     159-166                          153   0 0 cyclopropyl  C(CH.sub.3).sub.3                                                                          H  H     176-178                          154   0 0 CH(CH.sub.3)C.sub.3 H.sub.7                                                                C.sub.2 H.sub.5                                                                            H  H     147-149                          155   0 0 C(CH.sub.3)C.sub.2 H.sub.5                                                                 C.sub.2 H.sub.5                                                                            H  H     141-144                          156   0 0 C.sub.3 H.sub.7 -n                                                                         C(CH.sub.3).sub.3                                                                          H  H     172-175                          157   0 0 CH.sub.2 CH(CH.sub.3).sub.2                                                                C(CH.sub.3).sub.3                                                                          H  H     164.5-167                        158   0 0 n-C.sub.4 H.sub.9                                                                          C(CH.sub.3).sub.3                                                                          H  H     125-127                          159   0 0 C(CH.sub.3).sub.2 CH.sub.2 Cl                                                              C(CH.sub.3).sub.3                                                                          H  H     151-153                          160   0 0 CH.sub.2 CH.sub.2 cyclopentyl                                                              C.sub.2 H.sub.5                                                                            H  H     165-166                          161   0 0 CH(C.sub.2 H.sub.5).sub.2                                                                  C(CH.sub.3).sub.3                                                                          H  H     168-170                          162   0 0 CH(CH.sub.3)C.sub.3 H.sub.7                                                                C(CH.sub.3).sub.3                                                                          H  H     145-148                          163   0 0 CH(CH.sub.3).sub.2                                                                         C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          H  H     115-120                          164   0 0 CH.sub.2 CH.sub.2 cyclohexyl                                                               C.sub.2 H.sub.5                                                                            H  H     154-155                          165   0 0 cyclohexyl   C(CH.sub.3).sub.3                                                                          H  H     187-188                          166   0 0 CH(CH.sub.3)C.sub.3 H.sub.7                                                                CH(CH.sub.3)C.sub.3 H.sub.7                                                                H  H     111-115                          167   0 0 C(CH.sub.3).sub.2 C.sub.2 H.sub.5                                                          C(CH.sub.3).sub.2 C.sub.2 H.sub.5                                                          H  H     156-158                          168   0 0 pinonoyl     C.sub.2 H.sub.5                                                                            H  H     glass                            169   0 0 C(CH.sub.3).sub.2 C.sub.2 H.sub.5                                                          C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          H  H     120.5-123                        170   0 0 CH(CH.sub.3)C.sub.3 H.sub.7                                                                C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          H  H     glass                            171   0 0 cyclohexyl   cyclohexyl   H  H     217-219                          172   0 0 cyclohexyl   C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          H  H     153.5-157                        173   0 0 3-4-diCl-phenyl                                                                            C(CH.sub.3).sub.3                                                                          H  H     187-191                          174   0 0 CH.sub.2 O-2,4-diCl-phenyl                                                                 C(CH.sub.3).sub.3                                                                          H  H     163-165                          175   0 0 3,4-diCl-phenyl                                                                            C(CH.sub.3)C.sub.3 H.sub.7                                                                 H  H     107-114                          176   0 0 2,4-diCl-phenyl                                                                            C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          H  H     153-157                          177   0 0 CH.sub.2 O-2,4-diCl-phenyl                                                                 C(CH.sub.3)C.sub.3 H.sub.7                                                                 H  H     126-129                          178   0 0 C(i-C.sub.3 H.sub.7).sub.2 CH.sub.3                                                        C.sub.2 H.sub.5                                                                            H  H     n.sub.D.sup.30 1.5225            179   0 0 CH=CHCH.sub.3                                                                              C(CH.sub.3).sub.3                                                                          H  H     67-69                            180   0 0 CH.sub.2 CH=CH.sub.2                                                                       C(CH.sub.3).sub.3                                                                          H  H     159-161                          181   0 0 CH.sub.2 CH.sub.2 cyclopentyl                                                              C(CH.sub.3).sub.3                                                                          H  H     142-143                          182   0 0 CH.sub.2 CH.sub.2 cyclohexyl                                                               C(CH.sub.3).sub.3                                                                          H  H     141.5-143                        183   0 0 3'-pinonyl   C(CH.sub.3).sub.3                                                                          H  H     61-67                            184   0 0 2,4-diCl-phenyl                                                                            C(CH.sub.3).sub.3                                                                          H  H     182-184                          185   0 0 C(i-C.sub.3 H.sub.7).sub.2 CH.sub.3                                                        C(CH.sub.3).sub.3                                                                          H  H     62-66                            186   0 0 CCl.sub.3    CH(CH.sub.3)C.sub.3 H.sub.7                                                                H  H     121-126                          187   0 0 CF.sub.3     CH(CH.sub.3)C.sub.3 H.sub.7                                                                H  H     139-146                          188   0 0 CH(CH.sub.3).sub.2                                                                         CH(CH.sub.3 C.sub.3 H.sub.7                                                                H  H     156-157                          189   0 0 CH(CH.sub.3)C.sub.2 H.sub.5                                                                CH(CH.sub.3)C.sub.3 H.sub.7                                                                H  H     145-147                          190   0 0 C(CH.sub. 3).sub.2 CH.sub.2 Cl                                                             CH(CH.sub.3)C.sub.3 H.sub.7                                                                H  H     n.sub.D.sup.30 1.5145            191   0 0 CH.sub.2 C(CH.sub.3).sub.3                                                                 CH(CH.sub.3)C.sub.3 H.sub.7                                                                H  H     n.sub.D.sup.30 1.5078            192   0 0 CH.sub.2 CH(CH.sub.3)CH.sub.2 C(CH.sub.3).sub.3                                            CH(CH.sub.3)C.sub.3 H.sub.7                                                                H  H     n.sub.D.sup.30 1.5020            193   0 0 CH.sub.2 O-2,4-diCl-phenyl                                                                 CH(CH.sub.3)C.sub.3 H.sub.7                                                                H  H     182-184                          194   0 0 C(CH.sub.3).sub.3                                                                          C(C.sub.2 H.sub.5).sub.2 CH.sub.3                                                          H  H     131-134.5                        195   0 0 CH.sub.2 C(CH.sub.3).sub.3                                                                 C(C.sub.2 H.sub.5).sub.2 CH.sub.3                                                          H  H     133-135                          196   0 0 CH.sub.2 CH(CH.sub.3)CH.sub.2 C(CH.sub.3).sub.3                                            C(C.sub.2 H.sub.5).sub.2 CH.sub.3                                                          H  H     57-62                            197   0 0 CH.sub.2 CH(CH.sub.3)C.sub.2 H.sub.5                                                       C.sub.2 H.sub.5                                                                            H  H     123-126                          198   0 0 CH.sub.2 CH(CH.sub.3)C.sub.2 H.sub.5                                                       C(CH.sub.3).sub.3                                                                          H  H     134-136                          199   0 0 CH.sub.2 CH(CH.sub.3)C.sub.2 H.sub.5                                                       CH(CH.sub.3)C.sub.3 H.sub.7                                                                H  H     107-108                          200   0 0 CH.sub.2 CH(CH.sub.3)C.sub.2 H.sub.5                                                       C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          H  H     100-103                          201   0 0 CH.sub.2 CH(CH.sub.3)C.sub.2 H.sub.5                                                       CH.sub.2 CH(CH.sub.3)C.sub.2 H.sub.5                                                       H  H     132-134                          202   0 0 CH(C.sub.2 H.sub.5)C.sub.4 H.sub.9                                                         C.sub.2 H.sub.5                                                                            H  H     126-129                          203   0 0 CH(C.sub.2 H.sub.5)C.sub.4 H.sub.9                                                         CH(C.sub.2 H.sub.5)C.sub.4 H.sub.9                                                         H  H     53-70                            204   0 0 CH.sub.2 C(CH.sub.3).sub.3                                                                 CH(CH.sub.3)CH.sub.3                                                                       H  H     189-192                          205   0 0 C.sub.2 H.sub.5                                                                            C(C.sub.2 H.sub.5).sub.2 CH.sub.3                                                          H  H     134-137                          206   0 0 CH(CH.sub.3)C.sub.3 H.sub.7                                                                C(C.sub.2 H.sub.5).sub.2 CH.sub.3                                                          H  H     45-48                            207   0 0 CH.sub.2 C(CH.sub.3).sub.2 C.sub.2 H.sub.5                                                 C.sub.2 H.sub.5                                                                            H  H     174-175                          208   0 0 CH.sub.2 C(CH.sub.3).sub.2 C.sub.2 H.sub.5                                                 C(CH.sub.3).sub.3                                                                          H  H     156-157                          209   0 0 CH(C.sub.2 H.sub.5)C.sub.4 H.sub.9                                                         C(CH.sub.3).sub.3                                                                          H  H     132-134                          210   0 0 CH(C.sub.2 H.sub.5)C.sub.3 H.sub.7                                                         CH(CH.sub.3)C.sub.3 H.sub.7                                                                H  H     108-112                          211   0 0 CH(C.sub.2 H.sub.5)C.sub.4 H.sub.9                                                         C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          H  H     119-121                          212   0 0 CH.sub.2 C(CH.sub.3).sub.2 C.sub.2 H.sub.5                                                 CH(CH.sub.3)C.sub.3 H.sub.7                                                                H  H     135-136                          213   0 0 CH.sub.2 C(CH.sub.3).sub.2 C.sub.2 H.sub.5                                                 C(CH.sub.3)C.sub.3 H.sub.7                                                                 H  H     108-110                          214   0 0 CH.sub.2 C(CH.sub.3).sub.2 C.sub.2 H.sub.5                                                 CH.sub.2 C(CH.sub.3).sub.2 C.sub.2 H.sub.5                                                 H  H     175-178                          215   0 0 C.sub.2 F.sub.5                                                                            C.sub.2 H.sub.5                                                                            H  H     172-175                          216   0 0 C.sub.2 F.sub.5                                                                            C(CH.sub.3).sub.3                                                                          H  H     187-190                          217   0 0 C.sub.2 F.sub.5                                                                            CH(CH.sub.3)C.sub.3 H.sub.7                                                                H  H     126-128                          218   0 0 C.sub.2 F.sub.5                                                                            C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          H  H     112-114                          219   0 0 CCl.sub.2 CF.sub.3                                                                         C.sub.2 H.sub.5                                                                            H  H     141-143                          220   0 0 2-CH.sub.3 -phenyl                                                                         C(CH.sub.3).sub.3                                                                          H  H     185-186.5                        221   0 0 3-CH.sub.3 -phenyl                                                                         C(CH.sub.3).sub.3                                                                          H  H     163-164                          222   0 0 4-CH.sub.3 -phenyl                                                                         C(CH.sub.3).sub.3                                                                          H  H     206-207                          223   0 0 2-CH.sub.3 -phenyl                                                                         CH(CH.sub.3)C.sub.3 H.sub.7                                                                H  H     172-174                          224   0 0 3-CH.sub.3 -phenyl                                                                         CH(CH.sub.3)C.sub.3 H.sub.7                                                                H  H     68-72                            225   0 0 4-CH.sub.3 -phenyl                                                                         CH(CH.sub.3)C.sub.3 H.sub.7                                                                H  H     122-124                          226   0 0 2-CH.sub.3 -phenyl                                                                         C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          H  H     154-155                          227   0 0 3-CH.sub.3 -phenyl                                                                         C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          H  H     129-130                          228   0 0 4-CH.sub.3 -phenyl                                                                         C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          H  H     146-148                          229   0 0 2-Cl-phenyl  C(CH.sub.3 ).sub.3                                                                         H  H     185-187                          230   0 0 3-Cl-phenyl  C(CH.sub.3).sub.3                                                                          H  H     193-194                          231   0 0 2-Cl-phenyl  CH(CH.sub.3)C.sub.3 H.sub.7                                                                H  H     154-156                          232   0 0 3-Cl-phenyl  CH(CH.sub.3)C.sub.3 H.sub.7                                                                H  H     118-120                          233   0 0 4-Cl-phenyl  CH(CH.sub.3)C.sub.3 H.sub.7                                                                H  H     131-133                          234   0 0 2-Cl-phenyl  C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          H  H     128-130                          235   0 0 3-Cl-phenyl  C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          H  H     132-133                          236   0 0 4-Cl-phenyl  C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          H  H     135-137                          237   0 0 2-F-phenyl   C.sub.2 H.sub.5                                                                            H  H     186-187                          238   0 0 4-F-phenyl   C.sub.2 H.sub.5                                                                            H  H     205-206                          239   0 0 2-F-phenyl   C(CH.sub.3).sub.3                                                                          H  H     123-126                          240   0 0 4-F-phenyl   C(CH.sub.3).sub.3                                                                          H  H     195-196                          241   0 0 2-F-phenyl   CH(CH.sub.3)C.sub.3 H.sub.7                                                                H  H     129-131                          242   0 0 4-F-phenyl   CH(CH.sub.3)C.sub.3 H.sub.7                                                                H  H     141-143                          243   0 0 2-F-phenyl   C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          H  H     114-115                          244   0 0 4-F-phenyl   C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          H  H     147-149                          245   0 0 CH(C.sub.2 H.sub.5).sub.2                                                                  CH(CH.sub.3)C.sub.3 H.sub.7                                                                H  H     157-159                          246   0 0 CH(CH.sub.3)C.sub.3 H.sub.7                                                                CH(CH.sub.3)C.sub.3 H.sub.7                                                                H  H 3-Cl                                                                              63-66                            247   0 0 C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                                            H  H 2-CH.sub.3                                                                        266-267                          248   0 0 i-C.sub.3 H.sub.7                                                                          i-C.sub.3 H.sub.7                                                                          H  H 2-CH.sub.3                                                                        295-296                          249   0 0 t-C.sub.4 H.sub.9                                                                          t-C.sub.4 H.sub.9                                                                          H  H 2-CH.sub.3                                                                        260-261                          250   0 0 CH(CH.sub.3)C.sub.3 H.sub.7                                                                CH(CH.sub.3)C.sub.3 H.sub.7                                                                H  H 2-CH.sub.3                                                                        245-246                          251   0 0 C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                          H  H 2-CH.sub.3                                                                        176-177                          __________________________________________________________________________

Other examples of compounds falling within the generic formulaspresented herein, which are preparable by the above-described proceduresand which may be formulated into herbicidal compositions and applied asherein illustrated are:

    X   Y     R.sub.1     R.sub.2   R.sub.3                                                                            R.sub.4                                                                            Z                                   ______________________________________                                        0   S     H           H         H    H                                        0   S     C.sub.2 H.sub.5                                                                           H         H    H                                        0   S     C.sub.2 H.sub.5                                                                           C.sub.2 H.sub.5                                                                         H    H                                        O   S     C.sub.2 H.sub.5                                                                           cyclopropyl                                                                             H    H                                        O   S     CH.sub.2 Cl CH.sub.2 Cl                                                                             H    H                                        O   S     cyclopropyl n-C.sub.5 H.sub.11                                                                      H    H                                        O   S     CH=CHCH.sub.3                                                                             C.sub.2 H.sub.5                                                                         H    H                                        O   S     furyl       furyl     H    H                                        O   S     CCl.sub.3   C.sub.2 H.sub.5                                                                         H    H                                        O   S     phenyl      phenyl    H    H                                        O   S     cyclohexyl  cyclohexyl                                                                              H    H                                        O   S     benzyl      C.sub.2 H.sub.5                                                                         H    H                                        O   S     2,4-diCl-phenyl                                                                           C.sub.2 H.sub.5                                                                         H    H                                        O   S     4-NO.sub.2 -phenyl                                                                        C.sub.2 H.sub.5                                                                         H    H                                        O   S     3,4-diCl-phenyl                                                                           i-C.sub.3 H.sub.7                                                                       H    H                                        O   S     C.sub.2 H.sub.5                                                                           CF.sub.3  H    H                                        O   S     t-C.sub.4 H.sub.9                                                                         t-C.sub.4 H.sub.9                                                                       H    H                                        O   S     phenyl      phenyl    H    H                                        O   S     cyclohexyl  cyclohexyl                                                                              H    H    5'-Cl                               O   S     C.sub.2 H.sub.5                                                                           3-NO.sub.2 -phenyl                                                                      H    H                                        O   O     C.sub.2 H.sub.5                                                                           i-C.sub.3 H.sub.7                                                                       H    H    5'-Cl                               O   O     C.sub.2 H.sub.5                                                                           i-C.sub.3 H.sub.7                                                                       H    H    5'-Br                               O   O     C.sub.2 H.sub.5                                                                           i-C.sub.3 H.sub.7                                                                       H    H    5'-F                                O   O     C.sub.2 H.sub.5                                                                           i-C.sub.3 H.sub.7                                                                       H    H    5'-C.sub.2 H.sub.5                  O   O     C.sub.2 H.sub.5                                                                           i-C.sub.3 H.sub.7                                                                       H    H    5'-NO.sub.2                         O   O     C.sub.2 H.sub.5                                                                           i-C.sub.3 H.sub.7                                                                       H    H    5'-CF.sub.3                         O   O     C.sub.2 H.sub.5                                                                           i-C.sub.3 H.sub.7                                                                       H    CH.sub.3                                 O   S     C.sub.2 H.sub.5                                                                           CH(C.sub.2 H.sub.5).sub.2                                                               H    CH.sub.3                                                                           5'-Cl                               O   S     C.sub.2 H.sub.5                                                                           phenyl    H    CH.sub.3                                                                           5'-NO.sub.2                         O   O     CH.sub.2 C(CH.sub.3).sub.3                                                                C.sub.2 H.sub.5                                                                         CH.sub.3                                                                           CH.sub.3                                 O   O     CH.sub.2 C(CH.sub.3).sub.3                                                                C.sub.2 H.sub.5                                                                         CH.sub.3                                                                           H    5'-Cl                               O   O     C.sub.2 H.sub.5                                                                           i-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                           H    5'-CF.sub.3                         O   O     C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                         C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           5'-NO.sub.2                         O   S     C.sub.2 H.sub.5                                                                           i-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                           CH.sub.3                                                                           5'-CH.sub.3                         O   O     H           H         H    H    5'-NH.sub.2                         O   O     C.sub.2 H.sub.5                                                                           C.sub.2 H.sub.5                                                                         H    H    5'-NH.sub.2                         O   O     C.sub.2 H.sub.5                                                                           i-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                           CH.sub.3                                                                           5'-NH.sub.2                         O   S     H           H         CH.sub.3                                                                           CH.sub.3                                                                           5'-OCH.sub.3                        O   S     C.sub.2 H.sub.5                                                                           C.sub.2 H.sub.5                                                                         H    H    5'-OC.sub.2 H.sub.5                 S   O     C.sub.2 H.sub.5                                                                           i-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                           CH.sub.3                                                                           5'-OCH.sub.3                        S   O     C.sub.2 H.sub.5                                                                           i-C.sub.3 H.sub.7                                                                       H    CH.sub.3                                                                           5'-NH.sub.2                         S   O     CH.sub.3    i-C.sub.3 H.sub.7                                                                       H    H    5'-OCH.sub.3                        S   S     C.sub.2 H.sub.5                                                                           C.sub.2 H.sub.5                                                                         CH.sub.3                                                                           CH.sub.3                                                                           5'-OCH.sub.3                        S   S     C.sub.2 H.sub.5                                                                           C.sub.2 H.sub.5                                                                         H    H    5'-NH.sub.2                         O   O     CH.sub.2 OC.sub.2 H.sub.5                                                                 C.sub.2 H.sub.5                                                                         H    H                                        O   O     C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                          i-C.sub. 3 H.sub.7                                                                      CH.sub.3                                                                           H                                        ______________________________________                                    

Pre-emergence herbicide test. On the day preceding treatment, seeds ofseven different weed species are planted in individual rows using onespecies per row across the width of the flat. The seeds used are hairycrabgrass (Digitaria sanguinalis (L.) Scop.), yellow foxtail (Setariaglauca (L.) Beauv.), watergrass (Echinochloa crusgalli (L.) Beauv.),California red oat (Avena sativa (L.)), redroot pigweed (Amaranthusretroflexus (L.), Indian mustard (Brassica juncea (L.) Coss.) and curlydock (Rumex crispus (L.). Ample seeds are planted to give about 20 to 50seedlings per row, after emergence, depending on the size of the plants.The flats are watered after planting. The spraying solution is preparedby dissolving 50 mg. of the test compound in 3 ml. of a solvent, such asacetone, containing 1% Tween 20 (polyoxyethylene sorbitan monolaurate.)The following day, each flat is sprayed at the rate of 20 pounds of thecandidate compound per 80 gallons of solution per acre. An atomizer isused to spray the solution on soil surface. The flats are placed in agreenhouse at 80° F. and watered regularly. Two weeks later, the degreeof weed control is determined by comparing the amount of germination andgrowth of each weed in the treated flats with weeds in several untreatedcontrol flats.

The rating system is as follows:

- = no significant injury (0-15 percent control)

+ = slight injury (25-35 percent control)

++ = moderate injury (55-65 percent control)

+++ = severe injury or death (85-100 percent control)

An activity index is used to represent the total activity on all sevenweed species. It is the sum of the number of plus marks, so that anactivity index of 21 represents complete control of all seven weeds. Theresults of this test are reported in Table II.

Post-emergence Herbicide Test. Seeds of five weed species includinghairy crabgrass, watergrass, wild oats, Indian mustard, and curly dockand one crop pinto beans (Phaseolus vulgaris), are planted in flats asdescribed above for pre-emergence screening. The flats are placed in thegreenhouse at 72°-85° F. and watered daily with a sprinkler. About 10 to14 days after planting when the primary leaves of the bean plant arealmost fully expanded and the first trifoliate leaves are just startingto form, the plants are sprayed. The spray is prepared by weighing out50 mg. of the test compound, dissolving it in 5 ml. of acetonecontaining 1 percent Tween 20 (polyoxy-ethylene sorbitan monolaurate)and then adding 5 ml. of water. The solution is sprayed on the foliageusing an atomizer. The spray concentration is 0.5% and the rate would beapproximately 20 lb/acre if all of the spray were retained on the plantand the soil, but some spray is lost so it is estimated that theapplication rate is approximately 12.5 lb/acre.

Beans are used to detect defoliants and plant growth regulators. Thebeans are trimmed to two or three plants per flat by cutting off theexcess weaker plants several days before treatment. The treated plantsare placed back in the greenhouse and care is taken to avoid sprinklingthe treated foliage with water for three days after treatment. Water isapplied to the soil by means of a slow stream from a watering hosetaking care not to wet the foliage.

Injury rates are recorded 14 days after treatment. The rating system isthe same as described above for the preemergence test where (-), (+),(++), and (+++) are used for the different rates of injury and control.The injury symptoms are also recorded. The maximum activity index forcomplete control of all the species in the post-emergence screening testis 18 which represents the sum of the plus marks obtained with the sixplant species used in the test. The herbicide activity index is shown inTable II.

                  TABLE II                                                        ______________________________________                                        HERBICIDAL ACTIVITY** - SCREENING RESULTS                                     Compound                                                                      Number       Pre-emergence Post-emergence                                     ______________________________________                                        1            12            15                                                 2            2             12                                                 3            7             3                                                  4            1             0                                                  5            0             5                                                  6            9             5                                                  7            18            15                                                 8            15            18                                                 9            0             7                                                  10           0             8                                                  11           19            18                                                 12           11            16                                                 13           20            18                                                 14           17            15                                                 15           14            18                                                 16           0             13                                                 17           1             8                                                  18           0             9                                                  19           0             7                                                  20           0             10                                                 21           12            16                                                 22           12            15                                                 23           6             13                                                 24           6             12                                                 25           4             8                                                  26           8             9                                                  27           11            16                                                 28           9             14                                                 29           17            15                                                 30           21            17                                                 31           2             11                                                 32           0             8                                                  33           0             9                                                  34           9             16                                                 35           2             9                                                  36           9             15                                                 37           6             14                                                 38           20            18                                                 39           6             12                                                 40           11            12                                                 41           5             14                                                 42           10            12                                                 43           9             12                                                 44           8             18                                                 45           18            16                                                 46           8             11                                                 47           8             12                                                 48           6             12                                                 49           16            18                                                 50           5             12                                                 51           5             11                                                 52           6             12                                                 53           6             0                                                  54           12            12                                                 55           21            18                                                 56           19            17                                                 57           6             8                                                  58           0             2                                                  59           10            9                                                  60           21            18                                                 61           15            16                                                 52           7             12                                                 63           16            16                                                 64           14            15                                                 65           3             10                                                 66           20            17                                                 67           8             8                                                  68           21            18                                                 69           0             11                                                 70           14            15                                                 71           10            11                                                 72           21            18                                                 73           11            12                                                 74           12            11                                                 76           20            18                                                 77           12            15                                                 78           3             11                                                 79           21            18                                                 80           18            18                                                 81           19            18                                                 82           17            16                                                 83           18            18                                                 84           7             12                                                 85           6             7                                                  86           0             2                                                  87           19            16                                                 88           21            18                                                 89           9             12                                                 90           0             3                                                  91           11            16                                                 92           4             10                                                 93           8             18                                                 94           20            18                                                 95           19            18                                                 96           18            18                                                 97           11            18                                                 98           6             14                                                 99           19            18                                                 100          13            18                                                 101          19            18                                                 102          6             15                                                 103          12            18                                                 104          19            18                                                 105          20            18                                                 106          14            17                                                 107          17            18                                                 108          11            18                                                 109          6             12                                                 110          12            17                                                 111          12            18                                                 112          9             14                                                 113          21            18                                                 114          19            18                                                 115          20            18                                                 116          21            18                                                 117          5             18                                                 118          11            17                                                 119          9             14                                                 120          5             14                                                 121          0             1                                                  122          0             12                                                 123          12            17                                                 124          17            18                                                 125          10            18                                                 126          9             18                                                 127          15            18                                                 128          3             17                                                 129          9             16                                                 130          7             9                                                  131          7             11                                                 132          16            15                                                 133          8             9                                                  134          6             14                                                 135          6             11                                                 136          12            13                                                 137          14            15                                                 138          2             13                                                 139          14            14                                                 140          0             7                                                  141          14            18                                                 142          12            16                                                 143          5             12                                                 144          0             2                                                  145          6             12                                                 146          3             4                                                  147          21            18                                                 148          21            17                                                 149          8             12                                                 150          10            17                                                 151          7             16                                                 152          15            17                                                 153          16            18                                                 154          18            18                                                 155          16            18                                                 156          17            19                                                 157          19            17                                                 158          11            16                                                 159          15            14                                                 160          3             11                                                 161          19            18                                                 162          21            18                                                 163          21            18                                                 164          0             8                                                  165          9             16                                                 166          18            18                                                 167          11            13                                                 168          9             15                                                 169          21            17                                                 170          20            18                                                 171          0             0                                                  172          0             14                                                 173          0             15                                                 174          17            15                                                 175          8             16                                                 176          9             14                                                 177          9             16                                                 178          9             18                                                 179          18            18                                                 180          19            18                                                 181          2             12                                                 182          0             9                                                  183          6             8                                                  184          14            12                                                 185          13            9                                                  186          14            15                                                 187          19            18                                                 188          21            16                                                 189          20            16                                                 190          21            18                                                 191          21            18                                                 192          9             12                                                 193          5             10                                                 194          18            11                                                 195          13            9                                                  196          1             4                                                  197          20            16                                                 198          21            16                                                 199          21            15                                                 200          21            16                                                 201          19            14                                                 202          21            18                                                 203          0             6                                                  204          10            11                                                 205          21            17                                                 206          21            15                                                 207          18            18                                                 208          17            15                                                 209          13            17                                                 210          13            18                                                 211          6             13                                                 212          16            14                                                 213          13            5                                                  214          0             4                                                  215          20            18                                                 216          16            18                                                 217          15            18                                                 218          16            18                                                 219          17            18                                                 220          4             11                                                 221          7             14                                                 222          0             4                                                  223          3             11                                                 224          8             12                                                 225          2             14                                                 226          7             14                                                 227          9             15                                                 228          0             10                                                 229          11            10                                                 230          6             10                                                 231          8             12                                                 232          8             12                                                 233          5             11                                                 234          9             13                                                 235          9             14                                                 236          6             12                                                 237          7             6                                                  238          11            10                                                 239          15            16                                                 240          8             9                                                  241          9             11                                                 242          8             12                                                 243          10            14                                                 244          6             11                                                 245          19            18                                                 246          0             14                                                 247          6             5                                                  248          0             5                                                  249          5             5                                                  250          3             4                                                  251          6             7                                                  ______________________________________                                         21 = 85-100% control of all seven plant species tested pre-emergence.         18 -- 85-100% control of all six plant species tested post-emergence     

The compounds of the present invention are used as pre-emergence ofpost-emergence herbicides and are applied in a variety of ways atvarious concentrations. In practice, the compounds are formulated withan inert carrier, utilizing methods well-known to those skilled in theart, thereby making them suitable for application as dusts, sprays, ordrenches and the like in the form and manner required. The mixtures canbe dispersed in water with the aid of a wetting agent or they can beemployed in organic liquid compositions, oil and water, water in oilemulsions, with or without the addition of wetting, dispersing oremulsifying agents. The amount applied depends upon the nature of theseeds or plants to be controlled and the rate of application varies fromapproximately 1 to approximately 50 pounds per acre. One particularlyadvantageous way of applying the compound is a narrow band along a rowcrop straddling the row. In practice, the compounds are formulated withan inert carrier utilizing methods well known to those skilled in theart, thereby making them suitable for particular application.

The phytotoxic compositions of this invention are applied to the plantsin the conventional manner. Thus, the dust and liquid compositions canbe applied to the plant by the use of power-dusters, boom and handsprayers and spraydusters. The compositions can also be applied fromairplanes as a dust or a spray because they are effective in very lowdosages. In order to modify or control growth of germinating seeds oremerging seedlings, as a typical example, the dust and liquidcompositions are applied to the soil according to conventional methodsand are preferably distributed in the soil to a depth of at leastone-half inch below the soil surface. It is not necessary that thephytotoxic compositions be admixed with the soil particles and thesecompositions can be applied merely by spraying or sprinkling the surfaceof the soil. The phytotoxic compositions of this invention can also beapplied by addition to irrigation water supplied to the field to betreated. This method of application permits the penetration of thecompositions into the soil as the water is absorbed therein. Dustcompositions, granular compositions or liquid formulations applied tothe surface of the soil can be distributed below the surface of the soilby conventional means such as discing, dragging or mixing operations.

The phytotoxic compositions of this invention can also contain otheradditaments, for example fertilizers, pesticides and the like, used asadjuvant or in combination with any of the above-described adjuvants.Other phytotoxic compounds useful in combination with theabove-described compounds include for example 2,4-dichlorophenoxyaceticacids, 2,4,5-trichlorophenoxyacetic acid, 2-methyl-4-chlorophenoxyaceticacid and the salts, esters and amides thereof; triazine derivatives,such as 2,4-bis (3-methoxypropylamino)-6-methylthio-S-triazine;2-chloro-4-ethylamino-6-isopropylamino-S-triazine, and2-ethylamino-4-isopropylamino-6-methylmercapto-S-triazine, ureaderivatives, such as 3-(3,4-dichlorophenyl)-1,1-dimethyl urea and3-(p-chlorophenyl)-1,1-dimethyl urea and acetamides such as N,N - dially-α-chloroacetamide, N-(α-chloroacetayl)hexamethylene imine, andN,N-diethyl-a-bromacetamide and the like; benzoic acids such as3-amino-2,5-dichlorobenzoic and; thiocarbamates, such as S-propyldipropylthiocarbamate; S-ethyl-dipropylthiocarbamate,S-ethyl-cyclohexylethyl-thiocarbamate, S-ethylhexahydro-1H-azepine-1-carbothioate and the like. Fertilizers useful incombination with the active ingredients include for example ammoniumnitrate, urea and superphosphates. Other useful additaments includematerials in which plant organisms take root and grow such as compost,manure, humus, sand and the like.

The concentration of a compound of the present invention, constitutingan effective amount in the best mode of administration in the utilitydisclosed is readily determinable by those skilled in the art. Variouschanges and modifications are possible without departing from the spiritand scope of the invention described herein and will be apparent tothose skilled in the art to which it pertains. It is accordinglyintended that the present invention shall only be limited by the scopeof the claims.

What is claimed is:
 1. A method for controlling the growth of vegetationwhich comprises applying to the area where control of said vegetativegrowth is desired, a growth controlling amount of a compound having theformula ##SPC4##in which R₁ and R₂ are independently selected from thegroup consisting of alkyl containing from 1 through about 10 carbonatoms, inclusive, and lower alkenyl.
 2. The method according to claim 1in which R₁ and R₂ are independent alkyl groups.
 3. The method accordingto claim 2 in which R₁ is ethyl and R₂ is n-propyl.
 4. The methodaccording to claim 2 in which R₁ is 1,1-dimethylbutyl and R₂ is1,1-dimethylbutyl.
 5. The method according to claim 2 in which R₁ is1-ethylpropyl and R₂ is isopropyl.
 6. The method according to claim 2 inwhich R₁ is neopentyl and R₂ is ethyl.
 7. The method according to claim2 in which R₁ is neopentyl and R₂ is isopropyl.
 8. The method accordingto claim 2 in which R₁ is tert-butyl and R₂ is neopentyl.
 9. The methodaccording to claim 2 in which R₁ is 1,1-dimethylbutyl and R₂ isneopentyl.
 10. The method according to claim 2 in which R₁ is sec-butyland R₂ is ethyl.
 11. The method according to claim 2 in which R₁ issec-butyl and R₂ is sec-butyl.
 12. The method according to claim 2 inwhich R₁ is sec-butyl and R₂ is tert-butyl.
 13. The method according toclaim 2 in which R₁ is sec-butyl and R₂ is neopentyl.
 14. The methodaccording to claim 2 in which R₁ is 1-ethylpropyl and R₂ is ethyl. 15.The method according to claim 2 in which R₁ is 1,1-dimethylbutyl and R₂is ethyl.
 16. The method according to claim 1 in which R₁ is loweralkenyl and R₂ is lower alkenyl.
 17. The method according to claim 16 inwhich R₁ is 2,2-dimethylvinyl and R₂ is 2,2-dimethylvinyl.
 18. Themethod according to claim 1 in which R₁ is lower alkenyl and R₂ isalkyl.
 19. The method according to claim 18 in which R₁ is2,2-dimethylvinyl, R₂ is tert-butyl.
 20. The method according to claim18 in which R₁ is 2,2-dimethylvinyl, R₂ is 1,1-dimethylbutyl.
 21. Themethod according to claim 18 in which R₁ is 2,2-dimethylvinyl, R₂ isethyl.
 22. The method according to claim 18 in which R₁ is vinyl, R₂ isethyl.
 23. A method according to claim 2 in which R₁ is2,4,4-trimethylpentyl and R₂ is 1,1-dimethylbutyl.
 24. A methodaccording to claim 2 in which R₁ is 1-methylbuyl and R₂ is tert-butyl.